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Family-friendly vacation rentals in Guardistallo

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Guardistallo

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
An aerial view captures the sprawling vineyards and olive groves surrounding Podere Vergianoni. The property features a salt-water pool positioned on a terrace, offering panoramic views of the lush Chianti landscape and medieval castle in the distance. Rustic buildings line the garden area.
Condo in Noce
5 out of 5 average rating, 184 reviews

Ancient 17th-century farm in Chianti, Tuscany

Podere Vergianoni is an ancient and historic property dating back to the 17th century, located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional style of ancient Tuscany: wooden beams, terracotta floors, and tasteful handcrafted furnishings that will help you enjoy a pleasant stay. In the large outdoor courtyard, you'll find a saltwater swimming pool on a panoramic terrace with wonderful views of the castle, hills and vineyards, and breathtaking sunsets.

Top guest favorite
Apartment in Montescudaio
4.82 out of 5 average rating, 127 reviews

Casetta Sole with view over Tuscany Hills and Sea

Cozy rustic-Tuscan apartment in Montescudaio, Etruscan Coast. Carved from an ancient family winery cellar: cool in summer and warm in winter thanks to thick stone walls. Hilly location with stunning views over Tuscan countryside, olive groves, valley, and sea (15 min to beaches). Equipped kitchen, living room with sofa bed, double bedroom, shower bathroom. Private garden with table and sun loungers. Fast WiFi, AC, private parking. Ideal for couples or 3 people seeking authentic relaxation.

Guest favorite
A charming stone cottage is surrounded by lush greenery and tall trees. Two white lounge chairs are positioned on the manicured lawn, accompanied by a small round table. A sun umbrella offers shade, while large windows reflect natural light, showcasing the inviting interior.
Home in Montescudaio
4.96 out of 5 average rating, 123 reviews

Open space surrounded by nature

Casa Namaste is a small stone cottage with well-kept interiors 1 km from the medieval village of Montescudaio. The house is completely surrounded by woods and centuries-old oaks. 150 meters away flows the Cecina river. In the 5000 square meter garden there is a natural spring with a large stone tub to cool off and an outdoor hot shower surrounded by greenery. We have a Vodafone adsl line with download 33 and upload 1.4. Smart TV and air conditioning are also available starting this spring

Top guest favorite
A historic tower rises prominently against a blue sky dotted with fluffy clouds. Surrounding greenery complements the stone structure, with trees and small buildings visible along the hillside, collectively conveying a sense of tranquility.
Villa in Montecatini Val di Cecina
4.99 out of 5 average rating, 129 reviews

Belforti Tower

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

Top guest favorite
The exterior of the cottage is surrounded by greenery, featuring a sunlit terrace with a dining table and umbrella. Potted plants add color to the entrance, while the rustic charm of the stone and tiled details enhances the natural setting.
Home in Vaiano
4.99 out of 5 average rating, 259 reviews

Cottage in Toscana in antica Villa con giardino

Il Cottage è parte di una proprietà della famiglia Bernocchi, già presente nelle mappe della zona del 1500 ed e' situata proprio su di una antica via Romana che attraversava i monti della Calvana. Distante circa 9 km da Prato e 20 da Firenze. Il Cottage, liberi su tre lati, e' situato in posizione panoramica circondato da un parco privato, ideale per camminate e sport. Una vera e propria casa, con cucina, salotto, camera e bagno. Ampi spazi esterni, giardino e orto botanico.

Top guest favorite
Farm stay in Provincia di Siena
4.98 out of 5 average rating, 198 reviews

La Villa Farmhouse - Chestnut, Pool & Garden

Immersed in the green woods of the Senese hills, the beating heart of Tuscany, lies the La Villa estate. Characterized by a large park with swimming pool, gazebo, barbecue area and relaxation area, the farmhouse stands out for its strong link with the Tuscan tradition: a suggestive path will guide you to discover the woods surrounding the farm among olive trees and fields of lavender in bloom, among which you can forget the passage of time and enjoy the charms of nature.

Top guest favorite
A modern kitchen and dining area feature sleek cabinetry and a spacious dining table. White chairs surround the table, complemented by a vase of flowers. Large windows enhance the room's brightness, while neutral-colored tiles create a clean and inviting atmosphere.
Apartment in Montescudaio
4.93 out of 5 average rating, 165 reviews

Elegant and bright apartment in Montescudaio

The apartment has been recently renovated, very bright and welcoming, the furnishings are modern and practically new. Located in the residential area of Montescudaio, quiet and peaceful from where you can easily reach the most characteristic places of Tuscany: medieval villages, enchanting hills and all the splendid historic cities (Pisa, Florence, Siena...) that make Tuscany such a popular destination. Just 20 minutes to the sea. Your vacation will be unforgettable!

Top guest favorite
A spacious terrace is surrounded by lush greenery, featuring terracotta pots filled with plants. Comfortable wooden chairs are positioned to invite relaxation, overlooking scenic hills in the distance. A soft canopy provides shade, enhancing the tranquil atmosphere of this outdoor space.
Home in Peccioli
4.99 out of 5 average rating, 135 reviews

House with a breathless view in Tuscany

Halfway between Pisa and Florence, this dreamy Tuscan house is your perfect escape. Lounge on the panoramic terrace with sun-kissed views, sip your morning coffee, or enjoy al fresco dinners under the golden sunset. Nestled in the heart of a charming village turned open-air contemporary art museum, every corner feels like a picture-perfect moment. Peccioli is your gateway to Tuscany’s art cities or a serene hideaway to savor the magic of authentic local life.

Top guest favorite
A winding driveway is lined with tall cypress trees on either side. The green landscape stretches into the distance, revealing rolling hills and a distant rustic building surrounded by nature, creating a serene and inviting setting.
Home in Montaione
4.95 out of 5 average rating, 126 reviews

Cercis - La Palmierina

E' un appartamento facente parte di una tenuta completamente recintata di 60 ettari di natura incontaminata: più di 1000 ulivi, innumerevoli cipressi e foreste profumate creano un ambiente idilliaco per coloro che ricercano tranquillità e silenzi. La tenuta Palmierina è in prossimità di Castelfalfi (un vero gioiello di architettura medievale) e nelle vicinanze di Firenze (50 Km), Siena (50 Km), Pisa (50 Km). Nelle vicinanze ci sono due campi da golf.

Guest favorite
A serene garden area features two lounge chairs positioned on lush green grass, overlooking the sea in the distance. White lilies bloom in the foreground, complemented by a rustic shade structure nearby, providing a tranquil setting for relaxation.
Farm stay in Castagneto Carducci
4.95 out of 5 average rating, 151 reviews

Casa del Poggio, with a beautiful sea view

The Casa del Poggio (house at the hill) is located in the hills of Castagneto Carducci and is part of our organic farm. It is immersed in a peaceful countryside surrounded by olive groves, vineyards and woodland and enjoys a beautiful view of the sea and the castle of Castagneto Carducci. At the same time its position allows you to reach the village in just 10 minutes by foot and the beaches of Marina di Castagneto in 10 minutes by car or bus.

Guest favorite
A white umbrella provides shade over a small round table, which holds a potted cactus. In the background, rolling hills and olive trees are visible, accompanied by a swimming pool reflecting the sky. Lush greenery surrounds the area, enhancing the peaceful countryside ambiance.
Guest suite in Casale Marittimo
4.83 out of 5 average rating, 110 reviews

The cypress

New building of 30 square meters located in the context of property with independent main house immersed in the beautiful Tuscan countryside 12 km from the sea and close to centers of cultural interest. The beautiful villages of Bolgheri and Castagneto Carducci are easily accessible. Half anhour drive from Volterra. The furniture is brand new. Garden and pool with sea view with sea view available for guests to use.

Guest favorite
The agriturismo features a rustic exterior with earthy tones, framed by a large tree and a landscaped lawn. Stone pathways connect various outdoor seating arrangements, inviting relaxation while surrounded by nature. A patio area is visible, offering a cozy space for dining or leisure.
Farm stay in Sovicille
4.91 out of 5 average rating, 201 reviews

House at Gianni - Leccio

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Popular amenities for Guardistallo family-friendly rentals

When is the best time to visit Guardistallo?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$39,128 GYDG$39,336 GYDG$36,839 GYDG$33,300 GYDG$31,635 GYDG$35,382 GYDG$39,336 GYDG$46,621 GYDG$33,925 GYDG$35,590 GYDG$36,006 GYDG$44,331 GYD
Avg. temp7°C8°C10°C13°C17°C21°C24°C24°C21°C17°C12°C8°C

Quick stats about vacation rentals that are family-friendly in Guardistallo

  • Total vacation rentals

    Explore 120 vacation rentals in Guardistallo

  • Nightly prices starting at

    Guardistallo vacation rentals start at G$8,325 GYD per night before taxes and fees

  • Verified guest reviews

    Over 900 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Vacation rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Guardistallo vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Guardistallo rentals

  • 4.6 Average rating

    Guardistallo stays receive an average rating of 4.6 out of 5 from guests

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